Synthesis Of Pyrimidine Derivatives Research Articles

Synthesis, 18F‐Radiolabelling and Biological Evaluations of C‐6 Alkylated Pyrimidine Nucleoside Analogues

Synthesis of pyrimidine derivatives with a side‐chain attached to the C‐6 of pyrimidine ring (6–14) is reported. Target compounds 8 and 12 were subjected to in vitro phosphorylation tests, determination of their binding affinities to herpes simplex virus (HSV‐1) thymidine kinase (TK) and catalytic turnover constants. Fluorinated pyrimidine derivative 12 (40 µM) exhibited better binding affinity for HSV‐1 TK than acyclovir (ACV, 170 µM) and ganciclovir (GCV, 48 µM). Catalytic turnover constant (k cat) of 12 (0.08 s− 1) was close to the k cat values of ACV (0.10 s− 1) and GCV (0.10 s− 1). Furthermore, compounds 8 and 12 showed no cytotoxic effects in HSV‐1 TK‐transduced and non‐transduced cell lines. Besides, compounds 8 and 12 did not exhibit antiviral or cytostatic activities against several viruses and malignant tumor cell lines that were evaluated. The new fluorinated pyrimidine derivative 16 that is phosphorylated by HSV‐1 TK could be developed as non‐toxic PET‐tracer molecule. Thus, 18F labelling of the precursor 14 was performed by nucleophilic substitution using [18F] tetrabutylammonium fluoride as the fluorinating reagent.

ChemInform Abstract: Fluorocontaining 1,3‐Dicarbonyl Compounds in the Synthesis of Pyrimidine Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Fluorocontaining 1,3-Dicarbonyl Compounds in the Synthesis of Pyrimidine Derivatives

Hexafluoroacetylacetone reacts with urea (thiourea) to yield respectively 4,6-bis(hydroxy)-4,6-bis(trifluoromethyl)hexahydropyrimidin-2-one(thione). The dehydration of the products and also reaction of nonsymmetrical fluoroalkyl-containing 1,3-diketones with urea (thiourea) afford substituted pyrimidines. The condensation of fluorinated 3-oxoesters and 1,3-diketones with benzaldehyde and urea (thiourea) results in 5-alkoxycarbonyl(acyl)-4-hydroxy-2-oxo(thioxo)-6-phenyl-4-fluoroalkylhexahydropyrimidines that on dehydration furnish 5-alkoxycarbonyl(acyl)-2-oxo(thioxo)-4-phenyl-6-fluoroalkyltetrahydropyrimidines. Ethyl 7-nonafluorobutyl-5-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-6-carboxylate hydrobromide forms in reaction of dibromoethane with ethyl ether of 2-thioxo-4-phenyl-6-nonafluorobutyltetrahydropyrimidine.

Reaction of Ketene Dithioacetals with Thioamides. A Synthesis of Pyrimidine Derivatives

Reaction of Ketene Dithioacetals with Thioamides. A Synthesis of Pyrimidine Derivatives

1,2,4‐Dithiazoliumsalze als Ausgangsstoffe für Pyrimidinderivate mit Oxo‐, Thioxo‐ oder Aminofunktion in 4‐Stellung

Synthesis of Pyrimidine Derivatives Having Oxo, Thioxo or Amino Functions at Position 4 from 1,2,4‐Dithiazolium SaltsThe (thioaroylamido)acrylonitriles 2, obtained by reaction of 1,2,4‐dithiazolium salts 1 with ethyl cyanacetate, undergo ring transformation reactions by reaction with ammonium acetate, primary and secondary amines and form the pyrimidines 7–9. A possible mechanism for these reactions is discussed.

ChemInform Abstract: Synthesis of Pyrimidine Derivatives and Their Related Compounds Using Ketene Dithioacetals

ChemInform Abstract: Synthesis of Pyrimidine Derivatives and Their Related Compounds Using Ketene Dithioacetals

ChemInform Abstract: Synthesis of Pyrimidine Derivatives by the Reaction of Ketene Dithioacetals with Amides.

AbstractReactions of the ketene dithioacetals (Ia) ‐ (Ic) with the amides (II), benzamidine hydrochloride (V), thioacetamide (VII), or with the ureas (XI) are described as outlined in the reaction scheme.

Synthesis of Pyrimidine Derivatives and Their Related Compounds Using Ketene Dithioacetals

Reactions de dithioacetals de thiocetenes avec des composes a methylene actif, des carboxamides et des amides; reactions de Mannich; obtention de pyrimidines et de composes pyrimidiques bi- ou tricycliques

ChemInform Abstract: Activated Nitriles in Heterocyclic Synthesis. Synthesis of Pyrimidine Derivatives.

Synthesis of polyfunctional pyrimidine derivatives via the reaction of acrylonitrile derivatives 1a and b with α,β-unsaturated nitriles 2a–f has been reported.

Synthesis of pyrimidine derivatives by the reaction of ketene dithioacetals with amides

AbstractReactions of methyl 2‐cyano‐3,3‐bis(methylthio)acrylate (1a) with carboxamides 2a‐g in the presence of sodium hydride in a mixture of benzene and N,N‐dimethylacetamide took place displacement with the methylthio group to give the corresponding methyl 3‐N‐acylamino‐2‐cyano‐3‐(methylthio)acrylates 3a‐g which were readily converted to the corresponding pyrimidine derivatives at reflux in methanol in good yields. Reactions of 2‐cyano‐3,3‐bis(methylthio)acrylonitrile (1b) with the carboxamides 2a‐f gave directly pyrimidine‐5‐carbonitrile derivatives 7a‐f. Ketene dithioacetals 1a,b smoothly reacted with thioamide 2g or urea 2h,i to give the expected pyrimidine derivatives 9,10a,b. Polyfunctionalized pyrimidines, thus obtained, were also used for the synthesis of fused pyrimidine derivatives.

ChemInform Abstract: Activated Nitriles in Heterocyclic Synthesis: A Novel Synthesis of Pyrimidine Derivatives.

AbstractThe 3‐aminocrotonitriles (I) undergo 1 + 1 addition to the aromatic nitriles (II) to yield the pyrimidines (III).

Activated Nitriles in Heterocyclic Synthesis. Synthesis of Pyrimidine Derivatives

Abstract Synthesis of polyfunctional pyrimidine derivatives via the reaction of acrylonitrile derivatives 1a and b with α,β-unsaturated nitriles 2a–f has been reported.

Activated nitriles in heterocyclic synthesis: A Novel Synthesis of Pyrimidine Derivatives

AbstractThe reaction of 3‐amino‐2,4‐diethoxycarbonylcrotononitrile with cinnamonitrile derivatives afforded the pyrimidines 5a‐‐d and not the pyridines 4 as expected from literature. Similarly pyrimidines 5e‐‐h were produced when 3‐amino‐2,4‐dicyanocrotononitrile was treated with the same reagent. The structure was established based on MS and high resolution 1H‐n.m.r. spectroscopy.

Formylation products of thioamides. XIII. Reaction of N‐(3‐aminothioacryloyl)‐formamidines with amines – Synthesis of Pyrimidine Derivatives

AbstractN‐(3‐Aminothioacryloyl)‐formamidines 3 react with primary amines to give either 4(1H)‐pyrimidinthiones 6 or transaminated N‐(3‐aminothioacryloyl)‐formamidines 5. Alkylation of the latter compounds gives rise to cyclised 6(1H)‐pyrimidinimines 7. The 4(1H)‐pyrimidinthiones 6 can be S‐alkylated to 4‐alkylmercaptopyrimidinium salts 8. Subsequent substitution of the alkylmercapto group of the 8 results in the formation of 4‐aminopyrimidinium salts 9, which can also be obtained starting from the 3 by a reversed reaction sequence that is first by S‐alkylation to 3‐alkylmercapto‐2‐azapentamethinium salts 10 and subsequent reaction with primary amines.

Acetals of lactams and acid amides. 41. Enamino amides in the synthesis of pyrimidine derivatives

The reaction of α-cyano-β-dimethylaminomethyleneacrylamide with arylamines was used to synthesize α-cyano-β-arylaminoacrylamides, which react readily with dimethylformamide diethylacetal to give the corresponding N-dimethylaminomethylene derivatives. The latter undergo cyclization to 1-aryl-5-cyano-4-pyrimidinones when they are heated in dimethylformamide or acetic anhydride and to pyrimido-[5,4-c]quinolone derivatives when they are heated in glacial acetic acid.

Activated nitrites in heterocyclic synthesis: a new procedure for the synthesis of pyrimidine derivatives

A novel synthesis of pyrimidine derivatives via reaction of enamino-nitriles and -esters with trichloroacetonitrile is reported and the synthetic potential of the method is demonstrated.

Synthesis of Pyrimidine Derivatives Having Olefinic Substituents by Palladium-catalyzed Cross-coupling Reaction of Iodopyrimidines

Synthesis of Pyrimidine Derivatives Having Olefinic Substituents by Palladium-catalyzed Cross-coupling Reaction of Iodopyrimidines

Synthesis of pyrimidine derivatives by reaction of pyrylium salts with guanidine and compounds of the guanidine series

2,4,6-Triphenylpyrylium perchlorate reacts with methylguanidine to give 1-methyl-2-amino-4,6-diphenylpyrimidinium perchlorate, which undergoes the Dimroth rearrangement to give 2-methylamino-4,6-diphenylpyrimidine. 2,4,6-Triarylpyrylium perchlorates react with guanidine to give N-pyrimidinylpyridinium salts. Pyrylium salts react with aminoguanidine, sulfanilylguanidine, and symmetrical diphenylguanidine at one amino group to give the corresponding pyridinium salts.

Synthesis of pyrimidine derivatives by reaction of pyrylium salts with guanidine and compounds of the guanidine series

Synthesis of pyrimidine derivatives by reaction of pyrylium salts with guanidine and compounds of the guanidine series

Synthesis of Pyrimidine Derivatives

Upon treatment with hydrazine hydrate in ethanol, ethyl 5-bromorotate and 5 bromuracil-6-acetate were converted into the corresponding 5-hydrazino esters. An attempt to cyclize orotaldehyde hydrazone in acidic media failed to succeed, and its acyl derivatives were obtained as sole products.Uracil-6 -acetic acid was converted into uracil-6-acetic hydrazide through its esters. The hydrazide was then treated with carbon disulfide in pyridine to obtain 2- (5-uracilmethyl) -1, 3, 4-oxadiazole-5-thion. Uracil-6-acetic hydrazide was also treated with phenyl isothiocyanate in pyridine to form a semicarbazide, which was subsequently converted into 3- (6-uracilmethyl) -4-phenyl-1, 2, 4-triazole-5-thion through alkali treatment. Treatment of the acyl hydrazide with potassium thiocyanate in hydrochloric acid gave a bis- (acyl hydrazide). Similar treatment with potassium cyanate afforded N1- (6-uracilacety1) -semicarbazide, which was then cyclized, upon alkali treatment, into 1H, 2H-dihydropyridazo-C3, [3, 4-d] pyrimidine.